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$105+ Cheap flights from Chicago (CHI) to Winnipeg (YWG)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/1. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — YWG
abr 5 — abr 121
sáb 4/5
sáb 4/12
1 adult, Economy
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Cheap flight deals from Chicago to Winnipeg

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Winnipeg (YWG). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated março 31, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$216
(Justfly.com)

One-way from

$105
(Kiwi.com)

Popular in

February

Cheapest in

January

Average price

$635

Good round-trip deal

$562 or less

Good one-way deal

$203 or less
Provider with most accurate pricing for Chicago (CHI)-Winnipeg flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Winnipeg flights.
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From Chicago (CHI) to Winnipeg
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One-way flight from Chicago (CHI) to Winnipeg
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High demand for flights, 0% potential price rise
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Cheapest flight prices on average. 3% potential price decrease ($17 potential savings vs. average RT price).
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Average for round-trip flights in March 2025
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Price to beat on a round-trip flight from Chicago (CHI) to Winnipeg.
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Price to beat on a one-way flight from Chicago (CHI) to Winnipeg.
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Find flight deals from Chicago to Winnipeg

Cheapest flights from Chicago to Winnipeg
Explore the most affordable flight options available from Chicago to Winnipeg. Find the lowest fares from popular airlines and budget airlines, with prices last updated on março 31, 2025.

This Justfly.com deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb 5/315:30 pmORD - YWG
1 stop18h 11mWestJet
ter 6/108:30 amYWG - ORD
1 stop8h 14mWestJet
Deal found 3/30$216
This Kiwi.com deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
qua 5/1411:10 amORD - YWG
2 stops13h 21mMultiple Airlines
qua 5/218:30 amYWG - ORD
1 stop8h 14mMultiple Airlines
Deal found 3/30$257
This Gotogate deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
qua 5/149:17 pmORD - YWG
1 stop15h 52mAir Canada
qua 5/212:20 pmYWG - ORD
Nonstop2h 28mAir Canada
Deal found 3/29$428
This Kiwi.com deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
qui 5/88:30 amMDW - YWG
1 stop7h 58mMultiple Airlines
dom 5/1112:52 pmYWG - MDW
1 stop4h 53mMultiple Airlines
Deal found 3/30$437
This Delta deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb 5/316:00 amMDW - YWG
2 stops17h 25mDelta
qua 6/186:45 amYWG - MDW
2 stops14h 53mDelta
Deal found 3/30$447
This United deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb 5/317:58 pmORD - YWG
Nonstop2h 35mUnited Airlines
ter 6/102:20 pmYWG - ORD
Nonstop2h 31mUnited Airlines
Deal found 3/30$509
This Delta deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb 5/317:05 amORD - YWG
2 stops16h 20mDelta
sáb 6/146:45 amYWG - ORD
2 stops6h 04mDelta
Deal found 3/30$514
This Agoda.com deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Agoda.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
qua 8/139:20 amMDW - YWG
1 stop10h 48mWestJet
qui 8/218:50 amYWG - MDW
1 stop4h 12mWestJet
Deal found 3/29$574
This Porter Airlines deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
qua 6/49:40 amMDW - YWG
2 stops24h 46mPorter Airlines
ter 6/1711:45 amYWG - MDW
2 stops21h 00mPorter Airlines
Deal found 3/30$596

Cheapflights Fare Finder

Customize your flight search to find flights from Chicago to Winnipeg that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated março 31, 2025.
Use the filters below to find and compare flights from Chicago to Winnipeg that are best for you.

Fly from

Chicago

Fly to

Winnipeg

Route

Depart

Return

Price

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

sáb 5/31

5:30 pm-11:41 am

1 stop18h 11m

Winnipeg

ter 6/10

8:30 am-4:44 pm

1 stop8h 14m

$216

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

qua 5/14

11:10 am-12:31 am

2 stops13h 21m

Winnipeg

qua 5/21

8:30 am-4:44 pm

1 stop8h 14m

$257

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

qua 5/14

9:17 pm-1:09 pm

1 stop15h 52m

Winnipeg

qua 5/21

2:20 pm-4:48 pm

Nonstop2h 28m

$428

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

qui 5/8

8:30 am-4:28 pm

1 stop7h 58m

Winnipeg

dom 5/11

12:52 pm-5:45 pm

1 stop4h 53m

$437

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

sáb 5/31

6:00 am-11:25 pm

2 stops17h 25m

Winnipeg

qua 6/18

6:45 am-9:38 pm

2 stops14h 53m

$447

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

sáb 5/31

7:58 pm-10:33 pm

Nonstop2h 35m

Winnipeg

dom 6/15

2:20 pm-4:51 pm

Nonstop2h 31m

$509

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

sáb 5/31

7:05 am-11:25 pm

2 stops16h 20m

Winnipeg

sáb 6/14

6:45 am-12:49 pm

2 stops6h 04m

$514

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

qua 8/13

9:20 am-8:08 pm

1 stop10h 48m

Winnipeg

qui 8/21

8:50 am-1:02 pm

1 stop4h 12m

$574

ChicagoWinnipeg

MDW - YWG

MDWYWG

Chicago Midway

qua 6/4

9:40 am-10:26 am

2 stops24h 46m

Winnipeg

ter 6/17

11:45 am-8:45 am

2 stops21h 00m

$596

ChicagoWinnipeg

ORD - YWG

ORDYWG

Chicago O'Hare Intl

qui 5/1

5:30 pm-9:01 am

1 stop15h 31m

$105

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/30

Showing 1-10 of 18 results
1
2

Compare providers for flights from Chicago to Winnipeg

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Winnipeg in March.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago-Winnipeg flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Winnipeg flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Winnipeg flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-Winnipeg flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Winnipeg flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Chicago to Winnipeg

Have a flexible travel schedule? Discover the best time to fly to Winnipeg from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Winnipeg

What is the cheapest month to book a flight from Chicago to Winnipeg?

Currently, August is the cheapest month in which you can book a flight from Chicago to Winnipeg (average of $358). Flying from Chicago to Winnipeg in April is currently the most expensive (average of $506). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CHI to YWG?

Find hourly flight availability from Chicago to Winnipeg. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated março 31, 2025.

One of the essential ways to save on airfare from Chicago to Winnipeg is to remain as flexible as possible. Flights that are in the afternoon tend to be the most expensive. A flight in the evening could potentially save you up to 12% on airfare.

Weekly flight availability from Chicago to Winnipeg

Explore weekly flight availability from Chicago to Winnipeg. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated março 31, 2025.

The most flights from CHI to YWG are scheduled on a Monday (3 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (3 on average).

Rainfall in Winnipeg by month

Plan your trip to Winnipeg by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Winnipeg ranges from 0.8 - 3.1 inches per month. June is typically the wettest month, when rainfall can reach 3.1 in. January is typically the driest time to visit Winnipeg when rainfall is around 0.8 in.

Temperature in Winnipeg by month

Plan your trip to Winnipeg by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Winnipeg, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 68.0 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 3.2 F).

Reviews of airlines servicing Winnipeg

Get insights into the airlines that provide service to Winnipeg. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Winnipeg. Reviews last updated março 31, 2025.
See what other customers who have flown with Delta, Porter Airlines and United Airlines from Chicago to Winnipeg have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,899 reviews

Comfort

8.0

Overall

8.0

Boarding

8.2

Entertainment

7.9

Crew

8.5

Food

7.3

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Delta
8.0
Very good
7,899 reviews
Delta
8.0
Very good
7,899 reviews

Comfort

8.0

Overall

8.0

Boarding

8.2

Entertainment

7.9

Crew

8.5

Food

7.3

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Porter Airlines
7.9
Good
277 reviews
Delta
8.0
Very good
7,899 reviews

Comfort

8.0

Overall

8.0

Boarding

8.2

Entertainment

7.9

Crew

8.5

Food

7.3

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
United Airlines
7.4
Good
8,614 reviews
Delta
8.0
Very good
7,899 reviews

Comfort

8.0

Overall

8.0

Boarding

8.2

Entertainment

7.9

Crew

8.5

Food

7.3

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
WestJet
7.2
Good
2,789 reviews
Delta
8.0
Very good
7,899 reviews

Comfort

8.0

Overall

8.0

Boarding

8.2

Entertainment

7.9

Crew

8.5

Food

7.3

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Air Canada
7.0
Good
9,001 reviews
Delta
8.0
Very good
7,899 reviews

Comfort

8.0

Overall

8.0

Boarding

8.2

Entertainment

7.9

Crew

8.5

Food

7.3

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Winnipeg. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Winnipeg from Chicago?

    Most people fly into Winnipeg (YWG) if they book a flight to Winnipeg from Chicago. On average, Winnipeg has 3 inbound flights from Chicago per day from 2 airlines. Winnipeg is conveniently located just 4.6 mi from Winnipeg’s city center.

  • What are the cheapest airlines flying from Chicago to Winnipeg round-trip?

    Flying on WestJet is currently your cheapest option to Winnipeg, with prices starting at $216. Additional round-trip tickets that might be worth considering are offered by Air Canada and Delta, with the lowest prices starting at $425 and $447, respectively. These flights start at 62% lower than the current average price 3 months from now.

  • What are the cheapest airlines to fly from Chicago to Winnipeg one-way?

    One-way options have recently been found by users for as low as $105 on WestJet. Other airlines that offer cheap prices include Delta from $184 and United Airlines from $231 one-way.

  • What are the most reliable airlines from Chicago to Winnipeg?

    The top 3 most reliable airlines when flying from Chicago to Winnipeg are SkyWest Airlines (80%), Air Canada (80%) and United Airlines (80%).

  • What are the cheapest flights from Chicago to Winnipeg?

    The cheapest flight price from Chicago to Winnipeg is $157. On average you can expect to pay $409. The most popular route, (Chicago O'Hare Intl - Winnipeg), can usually be booked for $274.

  • Can I find deals for flights from Chicago to Winnipeg that include hotel bookings?

    Yes. In addition to deals on Chicago to Winnipeg flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Winnipeg?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Winnipeg.

  • Can I find deals for business class flights from Chicago to Winnipeg?

    Yes. Cheapflights offers flight deals from Chicago to Winnipeg by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to Winnipeg?

    Currently, August is the cheapest month in which you can book a flight from Chicago to Winnipeg (average of $358). Flying from Chicago to Winnipeg in April is currently the most expensive (average of $506). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Chicago to Winnipeg

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Winnipeg flights
Midway to Winnipeg flights
St. Louis to Winnipeg flights

Top 2 airlines flying from Chicago to Winnipeg

Discover the top 2 airlines that operate flights from Chicago to Winnipeg. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated março 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$232Average$617FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$535Average$666FlexibilityNo cancel feeOn-time69%
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